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Activation of Vinyl Iodides for the Highly Enantioselective Addition to Aldehydes
Author(s) -
DeBerardinis Albert M.,
Turlington Mark,
Pu Lin
Publication year - 2011
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201007351
Subject(s) - allylic rearrangement , reagent , chemistry , silylation , enantioselective synthesis , catalysis , organic chemistry , chlorine
Mild and tolerant : Vinylzinc reagents were directly prepared from the reaction of vinyl iodides with ZnEt 2 under mild reaction conditions. The compound ( S )‐ 1 was found to catalyze the addition of the vinylzinc reagents to a variety of aldehydes to generate structurally diverse allylic alcohols with high yields and enantioselectivities. This catalytic process can tolerate functional groups such as esters, chlorine, ethers, and silyl ethers on the substrates. acac=acetylacetonate, NMP= N ‐methyl‐2‐pyrrolidone.